Complicated
by existential1rony
Summary: The aftermath of a sniper case leaves Hailey analyzing her complicated feelings for both Jay and Adam. And leaves Jay evaluating the situation that they're all in together, whether they like it or not. Will a conclusion finally arise? Slow-burn Upstead
1. Chapter 1

_[A/N: This is based on the promo for the 6x17 episode involving the sniper. Depending how things go with Hailey, Jay, and Adam in the show, I think I'll continue to loosely base chapters in accordance with the rest of this season. We'll see how it goes... for the time being, hope this one suffices. Thanks for reading, as always!] _

* * *

Hailey Upton was sitting by her locker mulling over the days' events. They had caught the sniper, and at the end of the day, that should be all that mattered – that the cases were resolved with as minimal damage as possible. She wished that was all she could say was on her mind, but it wasn't. She thinks back to hours before when the sniper barely missed her, by the grace of luck Antonio getting to him first; the bullet landing a foot or so behind her into the empty office building. She remembers turning around to see Jay's worried face running toward her from across the park, then him suddenly halting. Next thing she knew, Adam was at her side asking her if she was okay and pulling her into a hug. She smiled and nodded at Jay from Adam's embrace, acknowledging to him that she was fine… and her heart broke a little more as she watched Jay give her one of his nods back and start to walk away.

Things between all of them have been more complicated recently, to say the least. She's been butting heads with Adam more and more as of late, and while the reasoning she's maintaining is his "mini-Voightness," she knows there's more to it than that… she just isn't ready to admit it fully yet. The bottom line being, her views will always align more with Jay's these days, then they will ever align with Adam's. Her and Jay have just grown together… as people, as partners, as friends… they've brought the best out in the other. She doesn't see that happening with Adam. She cares about him, and she knows he cares about her and that he has a huge heart, she just doesn't know if there's a real future there. She's always known. Just like she's always known that her feelings for Jay are just… _complicated_. There are so many different lines being crossed, and it's driving her moral-code soul insane. She never meant for things to get this far. She knows things have gotten worse since that case with Aidan, her and Jay have been even more in sync, and Adam has gone more off the rails. Jay just looks at her _differently_ now since that day… of course, if she's being really honest with herself, he's been looking at her differently since he found out about her and Adam. She's tried to convince herself it's all in her head though, it's the only way to keep her semi-sane.

When they finally got back to the precinct, Jay had come over to her, putting his hand comfortingly on her shoulder, and sharing a look that only the two of them can. He wanted to make sure she was okay, and she assured him she was. Everyone else came barreling up the stairs then, and the moment was over. Kim announced to everyone that they should go to Molly's and celebrate, and while most were on board, Hailey wasn't. Adam tried to get her to agree to go in private, but she politely declined and told him to have fun. He was hesitant at first, but didn't want to cause yet ANOTHER fight between them. Fast forward to now, Hailey finally slams her locker shut, and mind made up (before she changes it again), she runs outside to catch Jay at his truck before he leaves. He's opening the door when she runs over and looks a little surprised to see her.

"Hey…" Hailey says.

"Hey" Jay replies.

"You're not going to Molly's are you?"

"Nah, not if you're not. Not really in the mood to socialize, been a long day." He states simply.

"Yea, you're telling me…" she hesitates briefly, trying to talk herself through it. _It's just Jay, Hailey, breathe_! "…Pizza and beer at my place then?"

He gives her his token grin. "Sure. I'll grab the beer and meet you in 20?"

"Yea, sounds good!" she smirks back.

She starts walking to her car, unable to stop smiling to herself. She tries to calm her beating heart, telling herself it's just a normal night with her partner like always… but even her subconscious knows there's simply more to it now, no matter how much she wants to deny it…

* * *

Jay is sitting in his truck outside of Hailey's place trying to get his emotions in check before he goes in. The two of them haven't hung out as much since that night Adam called her while they were at the bar, neither emotionally ready for another awkward moment. And they really haven't spent a lot of outside time together since the Aidan case… Jay had felt an extra charge between them that day, and he needed to keep his distance. After all, no matter how he felt about her, she was with Adam, and he was his friend… and she was his _partner_. No, he had to get this in check, and fast. Something about the way she looked at him today though made him agree. That and the thought of almost losing her again, made him realize he'll take any and every moment he can get with her.

Jay lets out a heavy sigh. To say life has been unfair to him would be a bit of an understatement. He's been able to keep all of his triggers in check thanks to Hailey and her forcing him into getting help… he can do his best to block out the loss of his parents, the loss of Al, even the loss of Erin (though, he can honestly say that he's been over her for a long time now, also, thanks to his current _partner_)… but he's been finding it harder and harder recently to block the feelings he has for Hailey. It makes him angry in a way… angry that Adam was able to realize what he couldn't before him… angry that he's too damn unselfish… even angry that he's gone and fallen for another partner. He tries to convince himself things between them romantically would just end badly like they did with Erin… but he knows deep down that him and Hailey are more alike and compatible than anyone else he's ever met… and the fact he can't be with her is becoming too much for him to accept. But, that's a worry for a different time. Tonight, he's just glad he gets to spend some time with her like they always used to.

By the time he walks inside her place, the pizza delivery guy is minutes behind. They grab their beers and plates and go plop in front of her TV. The two of them are just quietly enjoying the other's company as they eat and sip their beers.

After wiping his mouth and taking another long chug of beer, Jay finally speaks.

"So, anything you want to talk about? "

Hailey gives him her trademark smirk. "Like what?"

"I don't know… like, oh, getting shot at? Or preferring to be on your couch with me and shitty beer over free shots?"

"I'm just glad you can finally admit that you buy shitty beer!" they both chuckle at her joke.

"But, seriously Hailey…"

"I'm fine, Jay, really."

They share one of their looks, and Jay has to force himself to turn away.

"Ok…"

"It's not like a bullet hasn't ever come at me before. Hell, I took one to the vest in an undercover and had to play dead until my unit busted in. " She tells him matter-of-factly.

"You never told me about that one before."

"Yea, it's supposed to be pretty under wraps…"

He starts laughing to himself.

"What's so funny?" she asks.

"Nothing, I'm just remembering the first time we met…"

She gives him her sarcastic, want-to-enlighten-me, look.

"You told me if you talked about your past you could get fired and not to be offended but…"

"…This is the first time in the back of your van…" she finishes for him and they both crack up.

"Wow! I forgot about that! No wonder you seemed to dislike me when I first joined the team." She says.

"What!? I never disliked you… I just figured you'd be a hard one to crack, much like someone else I may know…"

"Yea, good thing we're both open books, or else our partnership may have never worked!" she jokes and they both almost tear up from laughter.

"It was certainly a bumpy road, but I'm glad we were finally able to open up to each other, at least."

"Me too!…" she quietly whispers.

They stare at each other for a long time, the electric charge palpable between them. Neither is sure how long the moment lasts, but both know it's far too long for either of their sanities. Luckily the moment is broken by both of their phones vibrating. They open the group text and it's a picture from Kevin of Platt, Adam, Kim, and Antonio singing drunkenly on the faux-stage. They chuckle and breathe a sigh of relief for the interruption.

"Looks fun… maybe we should go and stop being so emo." Jay says.

"Yea, you're probably right. Let's go!" Hailey agrees and gets up from the couch.

She goes to grab their empty bottles the same time as Jay does and their hands graze… They both quickly pull back, trying to ignore and not feel the obvious spark. They swiftly get their stuff together to leave then, knowing they have to get the hell out of there… being alone together right now is far too complicated for either of them…

* * *

**[Disclaimer: It pains me that I have to do this because I sadly still have hope in humanity and morals, but alas... It's been brought to my attention that some people have been stealing my stories. I ONLY post on FanFiction and ArchiveofourOwn... so if you come across anything of mine on Wattpad or any of the socials, please report it. Thank you! And to the offenders, be better people!] **


	2. Chapter 2

Hailey is waiting in her living room for Adam to arrive. Today had been another doozy of a day and she knows it's only about to get worse. Hours before they had all been on a case involving a paranoid schizophrenic. They had gotten the intel on the guy's address and were sent to check it out. Jay and Hailey were to be the first ones to broach the house, while the others were going to question the neighbors. Within minutes of entering, they smelt gas. Jay with his quick army thinking told Hailey to run, and they both jumped out of the house just in time for it to explode around them. They landed on the pavement a couple yards away, with Jay on top of Hailey protecting her.

Luckily, physically they were both fine with the exception of a few cuts and bruises; emotionally, it was a different story. With Jay still on top of Hailey, they fell into the pattern they always do of conveying with their eyes all the emotions they were too scared to voice. Only this time, given the positioning of their predicament, it looked and felt even more intense than usual. There was even an instant there were Hailey thought Jay was going to kiss her… whether it was because he's been feeling what she has, or it was just the reactions of the moment, she didn't know… either way, it never happened, because soon enough Adam was staring over them. Adam, the guy she was supposed to be _dating_. He played it off well, just coughing to interrupt them, then quickly making sure they were ok, but she knew he was pissed. She's not entirely sure she blames him… after all, her heart was spoken for before they even hooked up, even if she didn't want to admit it.

She knows tonight will mark the beginning of the end… or maybe it's the end of the end… considering they weren't ever supposed to be serious to begin with. She wants to feel more upset about it, feeling like she owes Adam that much, but she's always known this was inevitable. She just hopes it's an adult discussion without much arguing. She can't handle much more today. Finally she hears the doorbell ring pulling her out of her thoughts and she runs to open it.

"Hey" she says simply as she steps aside to let him in.

Adam just nods at her as he walks in, not even giving her his usual hug or kiss on the cheek. _Oh boy… she was definitely right about where this conversation is going_.

"You want a beer or anything?" she offers.

"Nah, I don't think I'll be staying too long."

"Ok… well, you mind if I have one? Kinda feel like I may need it, y'know."

"Of course, it's your house."

"Adam…"

"Please Hailey, let me speak for once. You owe me that much!"

"Fair enough…"

"So I think it's time we talk about the elephant in the room. I thought I could ignore it because we were having fun, but I can't. In case you haven't noticed, I'm an all or nothing kind of guy… and I think it's time we end this before one of us gets hurt, most likely me."

"Adam, I'm not trying to hurt you."

"I know you're not Hailey, of course you're not… but you are… Can you honestly tell me with a clear conscious that you don't have feelings for Jay?"

"Adam…"

"No, seriously Hailey. It's ok, I get it. I mean, I kind of knew it before we hooked up anyway. But I'd appreciate if you admit it."

"What I do or don't feel for Jay doesn't matter. We're partners. We're great partners. And we're good friends. And both of us have been down that road before and swore never to again."

"You can run from your feelings all you want, but I can't do this anymore. I can't be the consolation prize. It's not fair to either of us… it's not fair to all three of us."

Hailey tears up a bit because she knows he's right and she wishes she never let things get this far. If only Jay never got shot, she would have been able to compartmentalize her feelings still. She would have never gotten with Adam to help with the blocking. The world works in mysterious ways though.

"I'm sorry, Adam, truly!"

"There's nothing to apologize for. I've been there." He shrugs. "Maybe I'm still there… we can all probably benefit from being more honest with our true feelings."

"Yea…"

"Well, as _fun_ as this conversation has been, I think I'm gonna go…"

She smiles as he tries to lighten the mood and walks back with him to the front door. As he opens it she says,

"I really did enjoy these past few months with you, y'know! Despite our occasional differences."

"Me too, Hailey. And for the record… it's pretty obvious that Jay has feelings for you too. I may not be the best advice giver when it comes to love, or my business anymore… but one of you should wake up soon!"

"Yea? Well, if we're giving advice… you should talk to Kim…"

"That's a chapter for a different time…" he smiles, and with that he walks away.

Hailey smirks and closes the door behind him. She feels a humongous weight lifted off of her shoulders, even if she's still not ready to deal with everything Adam said. She contemplates everything that transpired today for a few more minutes. Finally she decides she needs to get out of her place. She knows where she's going to end up, but doesn't want to think about the why of that just yet. Maybe one day. She grabs her favorite bottle of bourbon and heads out the door.

* * *

Jay is sitting on his couch pounding down his third beer. He can't stop himself from wishing it was with Hailey, especially after the hell of a day they had. He knows it's foolish though because she's supposed to see Adam tonight. He can't stop the wave of jealousy that washes over him and he swallows another big sip. In a way he's kind of grateful for Adam today… if it hadn't been for him coming over to them after the explosion, he's sure he would have kissed Hailey. What a mistake that would have been. He probably would have gotten punched by the both of them. He chuckles as he thinks that. Still, it would have been worth it to get to kiss her just once.

He can't believe how much harder it's been for him recently to keep his feelings for her under wraps. He knows that's what's best for everyone, but still, it hurts. Maybe he's just better off alone anyway. There's really only one person who understands and gets his issues, and the fact that she's his partner, & now taken, should be enough to deter him from love for a lifetime. He hears a knock at his door and wonders who it could be at this time of night, but equally grateful for the interruption. When he pulls back the door he's surprised to see who's behind it.

"Hailey, what are you doing here so late? Everything okay?"

She holds up her favorite bottle of bourbon and smirks at him as she walks in.

"Figured we could use some after the day we had…"

"Yea, but I thought…"

"Adam broke up with me, so, no." she quickly cuts him off.

Jay looks at her shocked, but secretly elated.

"What? Hailey, I'm so sorry!"

"It's fine. C'mon, it was bound to happen anyway."

"What? I thought you guys were doing good?"

"Jay, you wanna talk? Or you wanna crack this bottle? Because I'd much rather the alcohol right now." She says and she starts making her way to his couch. He grabs two glasses and is about to follow when he hears her again.

"Oh, I see you already got a head start!" she laughs looking at the near empty 6-pack on his coffee table.

They chuckle at each other as he makes his way over.

"Sorry, if I knew you were coming I would have saved you some."

"I mean, it's not every day one almost gets blown up. Sorry I didn't get the head start with you."

"So, you and Adam… should I even bother asking?"

"No…" they chuckle at each other and their predictability.

"Fair enough. Well, cheers to being alive… and single!" Jay says and they nod in agreement and clink their glasses.

"Yes, and _our thing_…" she says.

"At least I won't have to share my drinking buddy anymore!"

"C'mon Jay, y'know no matter what we'll always have this."

"There's probably not enough bourbon or tequila in the world."

"Yea, but then we can switch to rum or vodka…" she responds to him with her eyes twinkling. And they both realize that's enough, for now…

She yanks the remote from his hand as he rolls his eyes at her, and the two of them sit quietly into the night, keeping their feelings at bay… but both secretly enjoying each time one of their thighs brush up against the other.

* * *

[_A/N: Alright, I caved, it's just been too long without the show being on, so had to write some more. And I appreciate y'all baiting me to. Plus, I had some incredibly rare free time at work, so here we are. Well, now that Adam is out of the equation, that should pave the way for Hailey & Jay to get together, right?! You'd think... Don't worry, I have my final idea of where I'm going with this, but we'll see where the show takes us as well. Thanks so much again for reading, & for all the kind reviews! You guys are the best!] _


	3. Chapter 3

Jay was sitting in the truck with Hailey, staked out, deep in thought over the text message he received this morning. It was from someone he hadn't heard from in forever, someone he honestly wasn't expecting to hear from again, given the way things ended. It was Erin, and apparently the only reason she contacted him was because she didn't want him to hear secondhand from Voight or someone else. She was engaged… some hot shot FBI agent she met out in New York. All this information is something that would have destroyed him not a mere two years ago, MAYBE even a year or so ago… Now, he can honestly say that he's happy for her and he feels no loss from it at all. Obviously, they just weren't right for each other, even if it took him forever to see that.

It's not going unnoticed by him however, that he doesn't know if he would have ever come to this conclusion without meeting the person sitting next to him currently. Clearly, at first meeting Hailey he didn't feel this way… his life was consumed with losing Erin… but at the present, he can't picture his life without Hailey, not the former. Maybe it was just a part of moving on… or maybe his feelings for Hailey mean more now that he's older and more mature and knows what he needs out of life. He's not sure if he would have hit it off with Erin had he met her at this age or stage in his life… or maybe Hailey just guided him to get to that point… either way, it's both equal relief knowing for sure now that he's moved on from Erin; and distress at knowing how much he's fallen for Hailey. He's been weighing all these thoughts in his head silently, hoping Hailey won't notice, but of course that's a lost cause. She notices _everything_ about him… well, almost everything. As far as he knows, she's none the wiser that his feelings for her have turned more romantic than friendly.

"Hey, you okay? You've been awfully quiet this morning." Like clockwork, Hailey breaks him free of his internal speech.

"Yea, just thinking about some things, that's all."

"Anything you care to enlighten me with?" she smirks at him.

"I got a text from Erin this morning…"

"OH?..." she looks at him with a mix of shock, sympathy… and what seems like concealed curiosity.

"She's apparently engaged. Wanted me to hear it from her instead of Voight."

"Wow, ok, that's certainly out of nowhere… you alright?"

She tilts her head at him and he smiles at her, secretly thrilled she's always so genuinely concerned about him.

"Yea, I'll be ok."

"Jay…"

"Yea, yeah actually, honestly, I'm fine… didn't think I would be had this been last year… but I'm in a good place and happy for her."

"You sure? Because if you need to talk about it, y'know I'm here. Don't want you bottling everything up again." She says as she gently touches his arm.

"Hailey, I promise, I'm fine! I can't even remember the last time I thought about Erin!" he says so assuredly.

Hailey looks at him strange for a second, but quickly neutralizes her face again before he can question it.

"Ok, well if you wanna grab some beers tonight, just to process, y'know I'm free!" she jokes.

"I'm actually supposed to have dinner with Will tonight."

"Aww, brotherly bonding, you Halsteads are so cute!"

He grins and rolls his eyes at her. "You should come!"

"What? No… I don't want to intrude. We can catch up tomorrow. It's not like we don't see each other _all the time_ anyway!"

"Please, I want you to! Besides, Will could benefit by being around some females. I feel like I'm his only social experience since Natalie… and between you and me, it's getting kinda weird!" they both crack up.

"Alright, if you insist. I can probably meet you guys around 8:30. I told Kim I'd hit the gym with her before her date."

"Who goes to the gym before a date!?" he asks.

She laughs and shrugs, but says, "We can't all be as chiseled as you, Jay. Girls gotta work for it!"

"Yea, I'm sure you girls have such trouble!" he raises his brow at her flirtatiously, and they share a look… he quickly breaks out of it by continuing on. "But great, we're meeting at 8, so we'll scoop up a table and be ready for when you get there."

She nods her head in agreement as their radios go off. Perfect timing.

* * *

Jay and Will are sitting at a high-top waiting for Hailey to arrive. Jay can't wait for her to get there because he's growing tired of Will's constant prodding. And naturally, he just wants to see _her_.

He really has to figure out how to get better control over these thoughts. Even though her and Adam aren't together anymore, she's still his partner. And it still is not a line she'd probably ever try to cross, nor given any clear indication that she'd even want to, outside of what he feels is just wishful thinking on his part.

"So you're really fine with this Erin thing?" Will asks.

"Yea bro, for the _hundredth_ time… I'm happy for her!"

"Hmm, I wonder why that is?"

"What do you mean?"

"I just find it kind of curious that your ex you sulked over is engaged and you're completely unphased… all the while you're spending an extreme amount of time with Hailey."

Jay rolls his eyes at his brother.

"Not this again, I've told you, Hailey and I are just friends!"

"Yea, _just friends_ who are always together, _just friends_ whose favorite drink you know & order for before she arrives. You never order my drinks!" Will points at the random craft beer sitting next to Jay's.

"We're partners. It's my job to know these things."

"Really? I didn't know Detective Protocol 101 was knowing your partner's food preferences." Will jokes.

"Shutup Will. Look, Hailey and I are partners ok… can we just leave it at that for now please. I don't want to get into this… besides, she'll be here soon!"

Will nods his head up and points his gaze behind Jay. "Right again, I guess _just friends_ sense each other's timing as well…"

Jay shoots him a murderous look imploring him to drop it as Hailey walks over to them right at 8:30 on the dot.

"Hey guys!" she says cheerfully as she sits down next to Jay. She notices her favorite beer and exclaims, "Oh, thanks Jay, I could use this after the workout Kim made me do." She smiles and takes a long gulp, missing the pleading look Jay throws at Will.

"And thanks for letting me crash, Will. I hate to interrupt bro-time!"

"Oh anytime Hailey! I see this jackass enough!"

"Thanks bro, I love you too!" Jay responds and they all share a laugh.

"So Hailey, what have you been up to? Besides keeping my brother out of trouble."

"It's a hard job, but someone has to do it!" she smirks.

"Cheers to that!" Will says as he clinks his beer with Hailey's.

"Y'know, I am sitting right here!" Jay shakes his head grinning.

"Oh, we know!" they say in unison and crack up.

The waiter comes over to take their orders and offer another round, which they gladly take him up on. The three of them just joking and catching up. Jay can't help but smile at how well Hailey gets along with Will and most people in his life. They take to her so naturally and she always seems genuinely interested to learn more about them and know how they're doing. He knows it's part of her personality, but he also can't help but wonder if a small part of it has to do with him. There goes his wishful thinking again.

"So Hailey, as someone who is going through a particularly rough breakup, any advice you can spare me on how to move on?" Will randomly asks.

"Oh, I doubt I'm the person for that advice department…"

"I just figured since you and Adam broke up relatively recently, not to bring that up, I'm sorry."

"No, it's ok. I mean, my relationship with Adam wasn't anything close to yours & Natalie's, so I think I'm in a different place."

"Interesting…" Will says as he shoots Jay a look.

"You mind if I ask why you two broke up?" he continues.

Jay senses Hailey quickly tense up next to him.

"WILL! Seriously, man?" Jay says.

"No it's ok… typical question…" Hailey says and pauses for a while, contemplating her words.

As mad as Jay is that Will asked, he's quite curious to see what she has to say.

"We were having fun, and it just made sense to end it before things got too serious. The inter-office stuff probably wasn't the best idea…" she finally responds.

Jay feels his heart deflate right then and there. And this is exactly why he can't risk having her find out about his true feelings for her. It's just too complicated.

"Makes sense. Well, I'm sorry it didn't work out. I like Adam, I do… but you can do wayyy better than him in my doctoral opinion!" Will says jokingly.

"Adam's a good guy. He's just not for me." Hailey shrugs nonchalantly.

"Yea, he's certainly no Jay!" Will responds.

Hailey quickly blushes and tries to hide it. Jay's eyes almost bug out of his head.

"WILL!" Jay reprimands.

"What? You're my brother, of course you're awesome, you're related to me! And this is my fourth drink… and I hardly get out anymore… What!?"

Jay shakes his head rolling his eyes as Hailey looks completely amused.

"Man, I have to come out with you Halstead's more often, this is better than a show!" Hailey grins.

"Yea, that's not gonna happen. I think this was enough to last me a year!" Jay exclaims.

"Will's not wrong Jay, you are pretty great! …but I've also had a few drinks and will blame it on the alcohol if you ever gloat & bring it back up!" she looks at him with her eyes twinkling, only to quickly turn away and take another long gulp.

Jay and Will exchange intrigued looks and Jay knows he's gonna hear about this now for a million years. He can't help the boyish giddiness that arises in him though. _She thinks I'm great_. Wishful thinking restored…

* * *

_[A/N: Just another quick update... The hiatus inspired me, been way too long without Hailey & Jay time. Hopefully the return of the show this week will provide even more content on where else to take this story; *crosses fingers* for some Upstead goodness. Thank you kindly for all the wonderful comments and for following along!] _


	4. Chapter 4

Jay and Hailey were sitting in Starbucks enjoying a few moments of peace and coffee before starting their shifts. The past few weeks have been extra busy in Intelligence. Both are just enjoying this little bit of early morning down time that is so rare these days, and it doesn't hurt that they're spending it together.

Jay takes a sip of his coffee and looks Hailey over as she's staring out the window.

"Heard you bought Severide and Kidd's drinks the other night." He says.

She smiles at him, clearly amused. "Man, word travels fast!"

"Well, when you're talking free drinks, it always does." He smirks back at her.

"You a little jealous there, Jay?" she raises her brow at him.

"Maybe, just a little…" he grins and she gives him her wide-eyed questioning look.

"Not for the drinks, just that you didn't call me after that case. Sounded brutal from what I heard. Two malnourished kids basically trapped in a cage…"

"Yea, the ones with kids are always the hardest… but they adored Stella, she really made them feel safe. If it wasn't for her, who knows how long that bastard would have continued on. It was nice to see Severide back her, they seem like they're always there for each other, despite everything."

It doesn't go unnoticed by Jay or Hailey the double-meaning behind her last sentence, and they both nod at each other in understanding.

"That's great! I'm glad it all worked out. Even if you left your partner off the free drink list!" he jokes with her, but a part of him did really miss not having that night with her.

She rolls her eyes at him to deflect. "Don't worry Jay, I'll buy you a beer tonight!"

"Y'know I'm gonna hold you to that!"

She hears him say as she starts thinking. Even though they're only joking with each other, if she's being really honest with herself it did feel weird being out without him the other night. Sure, she only went to Molly's to pass on her thanks to the firefighters, and then hung out with some old coworkers she saw; but it was a little disappointing not having Jay there with her. She had almost called him, but she felt like the two of them had been spending an abundance of time together since her breakup with Adam. And the fact that Jay was the whole reason behind the breakup, despite not announcing it out loud, made her brain feel like she should take _some _space. It had been a fun night, but sadly for her heart's sake it still wasn't near as good of a time as she has when she's with him. She hears him break through her thoughts again.

"C'mon, we should probably go before we're late. Don't want to piss off Voight this early in the day."

"Yea, you're right, or else I'll have to pay for more than one beer for you tonight, and I'm not made of money."

"And here I thought your Lake Forest upbringing would always shine… I'm gonna have to get myself a different suga-partner!" he winks at her as they start walking out.

She lightly hits his arm laughing. "Keep it moving, Halstead, before you start to piss me off!"

They chuckle as they make their way to his truck and head over to the station. Once they arrive, they barrel up the steps together to start the day. Adam and Antonio are already at their desks, and Adam locks eyes with Hailey as she passes, giving her a knowing look. She shakes her head slightly at him, figuring what he's thinking and hopes no one else notices, especially Jay. It takes her back to months before when she was sleeping with Adam and refused to show up to work with him, in fear of people suspecting. She knows it means something that she doesn't feel this same way with Jay… part of her tells herself it's because they're not sleeping together, so it wouldn't matter what people thought… but the other half of her knows it's because she wouldn't care if people thought she was with Jay. Which is a troubling notion because isn't that one of the main reasons she doesn't want to admit her feelings? Because they're partners, and there's a line, and it's complicated? If she doesn't care what the others think about her and Jay, that certainly takes away one of her excuses to keep running from it…

"Hey, everything okay? You suddenly seem off…" Jay says to her across their desks, obviously noticing the pensive look she must have on her face.

How do they do this, read the other so well? She knows it goes deeper than just being perceptive detectives. It's unnerving how well they know each other.

"Yea, everything's fine. I just remembered I still have to write up all the paperwork with the Stella case. So much for an easy start to the morning." She responds, hoping to sell the partial lie.

"Well, since I'm such a gentleman, I'll buy you a beer tonight too… or maybe a slice of pizza, whichever's cheaper. Some of us grew up in the poorer side of Chicago y'know."

She throws her pen at him. "You're really in a teasing mood today, looking for a kick in the ass I see."

"Y'know Hailey, plenty of women would find me charmingly amusing."

"Yea? Maybe you should go find one of them to annoy. They've really been lining up!" she teases back.

"Nah, I'd much rather get my free beer from you. Plus, I doubt I can find someone else to give me as sarcastic of a smirk. It's what my dreams are made of!"

Even though they both know he's kidding, there's something slightly serious in the inflection of his voice as he says it, and they know they have to stop the flirting right then. They're at work, and things are confusing and complicated enough. Still, Hailey can't stop the small smile from forming thinking about him actually dreaming about her. Yeah, she's definitely running out of excuses…

* * *

_[A/N: Sorry for a shorty chapter, but wanted to jam an update in since the show returned. No real Upstead moments in this episode, and only 5 more to go this season, with probably not much Jay/Hailey in next episode either... so hopefully they make up for it in the final 4! Anyway, thanks so much for reading! Also, if you have any questions or requests, there's now a link in my profile to submit them, all anonymous! Let's discuss!] _


	5. Chapter 5

Jay is sitting in his apartment having a beer with Will. Normally he'd like to say he's enjoying this brotherly bonding time, but not tonight. No, tonight, Will is trying to convince him to go on a double-date with him. Actually, 'begging' would be the appropriate term. Some girl Will met at the hospital agreed to go out with him if she could also bring her single friend along. Naturally, Will figures he can rope him in. Jay wants to believe he's hesitant because he hates blind dates, especially doubles, but deep down he knows more of it has to do with Hailey. Which is stupid when you think of it because him and Hailey aren't together, have never been. Why should he let his feelings for his partner interfere with meeting other women!? He takes a big gulp then, knowing he doesn't want to contemplate that thought for much longer.

"Oh c'mon, it will be good for the both of us! Stop being such a stiff!" Will pleads.

"It's just not my thing man. I don't even know this girl, why would I want to go out with her? And with YOU there, seriously?"

"Because she's attractive… and at this point you haven't gotten laid since the first 'Avengers' movie came out!" Will jokes.

"Very funny… I am perfectly fine with being single right now."

"Yea right, if Hailey came waltzing in that door now and confessed her love for you, you'd practically put a ring on it before you could get the words out."

Jay gives him a death stare. He still does not want to discuss his relationship with Hailey with him. His feelings are complicated enough as is. He's certainly not going to confirm, or voice them to his brother.

"Not this again, Will. I told you, Hailey and I are friends, can we please leave it at that!?"

"Alright, whatever. But y'know, maybe seeing you with another girl will make her realize you are in fact, still interested in women. Jealousy is a powerful drug."

Jay rolls his eyes at that, but he must admit he is a bit intrigued. He can't help but wonder how Hailey would react if he was dating someone. He's well aware of how he reacted to her being with Adam. Still, it's not his style.

"Will, you're like a 17-year old sometimes, y'know that?"

"I'm just saying… anyway, c'mon Jay, I need this, do it for me!"

"Just tell this girl you're not into double-dating, especially on a first date. I'm sure she'll understand… who brings a friend along anyway?"

"She said her friend was going through a tough time and that she'd feel guilty going out and having fun without her."

"Oh great, you're really selling it now Will!" Jay jokes.

"Look, you do this for me and I swear to never bring up the Hailey thing again. You go on living in your denial world without my prying!"

Jay seriously ponders Will's request this time. It's frustrating enough sorting his feelings for Hailey on his own, let alone when Will tries to question him five times a week about it. What's the worst that can happen, it's just one date? Hell, maybe he'll actually like the girl and can move on from constantly wanting to be with his partner. He knows in his heart that's not going to happen, but a guy can hope, right? It's not like Hailey is going to be making a move on him anytime soon, or ever! He can enjoy himself in the meantime and get Will off his back.

"Okay, deal!" Jay extends his hand to shake Will's.

"Pleasure doing business with you!" Will smiles, clearly pleased. Jay sincerely hopes this won't be a mistake. He takes another long sip of beer as Hailey crosses his mind again.

* * *

Hailey studies Jay as they sit in the squad car for an extra overtime shift. It's been weeks now since her and Adam broke things off, and if anything, her feelings for Jay have gotten even more confusing. The two of them are still spending a good amount of time together, and she just can't seem to shake the feelings off. It was one thing when she was still with Adam, at least she could _pretend_ that he was the guy she was truly interested in… but now, she practically has no distraction from it. And it's certainly not like her and Jay has dared to address the elephant in the room aloud. She's actually starting to question if she should broach the subject one day, just to get it off her chest finally. But for the life of her she just can't seem to get ready to.

"So I had another interesting conversation with Will last night." She hears Jay say to her.

"Oh yea? What now?"

"He wants me to go on a double-date with him and some girl he met at Med." He says, and for a moment Hailey swears it looks like he's gauging her reaction to that.

Seconds go by and she still doesn't know how to respond, feeling a massive wave of jealousy spread through her. Why should she be jealous? It's not like her and Jay are together, and it's just a date. He had to see her with Adam all those months. Besides, it's like she's been trying to convince herself these past couple years, they're partners… and they shouldn't cross that line, especially with romantic entanglements. So why is she so disappointed? This could finally help settle whatever feelings they're burying deep down and clearly avoiding.

"Oh? Well, that's certainly interesting… did you tell him you would?" she finally responds.

"I did, yea. After much debating, I finally agreed, but I'm still not sure I want to. What do you think I should do?"

"Jay, I don't think it's my place… it was one thing with Camilla telling you what to do since it involved the job… but I probably shouldn't get involved with your average dating life." She says, really hoping to avoid the subject altogether.

"Your opinion means a lot to me, Hailey… and I just thought you might have some other input I'm not seeing…" he says to her hesitantly.

She wonders if he's trying to make her catch that double-meaning, but for her sanity at the moment she does her best to not over-analyze it. While they very well may need to talk about _them_ one day, on the job and stuck in a car is certainly not the time or place.

"I mean, it's just a date Jay, right? What's the big deal?" she says while looking down, picking at her finger and avoiding his eyes.

"So you think I should go then?"

"Maybe, if you want to. At the very least, it'll get you out of depressingly drinking shitty beer with me for a night." She tries to make a joke, and they stare at each other smirking. Their gaze lasts for a while, and Hailey contemplates saying something else, but hesitates. Jay waits, expecting more, but when he doesn't get it he finally just nods back at her.

"Guess you're right. I'm making a bigger deal of it than I should…" he finally responds, slightly melancholy.

Hailey doesn't know what to say anymore. It's all just too complicated. Her heart wants to scream at him and tell him to go out with her instead, but her stubborn head knows she can't. She thinks that Adam would kill her right now for missing this opportunity to have _that_ talk with Jay… but that's how they always differed. Adam loves wearing his heart on his sleeve, and as for her, she'll do anything to keep hers trapped in a hoodie. Luckily Jay takes pity on them both at the moment and changes the subject completely.

"So you still down to meet everyone at Molly's tonight once we get off?"

"Yea, we probably should. It's been too long…" she says, this time her voice laced with a double-entendre. They sit there quietly for the next hour, neither wanting to reveal any more than they already have. The tension between them obviously getting more palpable by the day. They're nothing but consistent at least, Hailey ponders sadly as she stares out the window.

* * *

_[A/N: Apologies for an angsty one, but I need this to help set up something in a future chapter. Hoping the show gives us some good Upstead moments when it returns to loosely base things on before I epilogue this particular story. Well, if I'm being honest, I'm just hoping for more Upstead moments in general leading to them getting together by season 7, haha! Thank you again for all the incredibly kind reviews & continuing to read, it means a lot!] _


	6. Chapter 6

The team had all decided to go play bowling to decompress some before doing the usual Molly's trip. It was something different, and great for all of their slight competitive natures. They decided to split into two groups to compete against each other. Naturally, Kevin, Kim, and Adam teamed up… pitting them against Antonio, Hailey, and Jay; losers buying the drinks later. Normally this setup would be ideal, natural, and fine with Hailey… but since the conversation with Jay a few hours prior, she's still a little uneasy. They didn't bring up Jay's date again for the remainder of their shift, and afterward when Jay dropped her off at her house to get ready, things were slightly more tense than average. By the time her and Jay arrived at bowling, they were determined to act like nothing was amiss, at least, she certainly was. The last thing she needs is for jealousy to rear its ugly head. As for Jay, the conversation left him seriously reconsidering the date-deal with Will. Even if Hailey is too stubborn to admit it, the last thing he wants to do is hurt her… or maybe that's just his wishful thinking again. Who knows? She may not care at all who he dates. It's leaving them both with a lot of contemplating and strategizing that has nothing to do with the best angle to throw a strike.

"Damn, I never realized how bad you two suck at bowling. I feel sorry for Antonio, he's about to lose his wallet on liquor!" Kevin says to them from the other lane, as Hailey throws another gutter ball.

"Yeah, how did I end up drawing the short straw? I figured you guys would be the best at this!" Antonio jokingly admits.

Before Hailey or Jay can respond, Kim and Adam's screams interrupt them as she throws a strike, and they embrace jumping up and down.

"Yea! That's my A-Team!" Kevin yells as he goes running over to jump with them as well.

"Oh, c'mon!" Antonio lifts up his arms in shock and dismay.

Hailey shrugs her shoulders at Jay as she walks back to grab her ball for her second attempt this turn.

"Sorry man, we're gonna step this up right now, I swear!" Jay announces to Antonio as he goes to walk over to Hailey. He gets close enough to whisper in her ear, a movement that makes them both shiver for a second.

"You knock all the pins on this one, and coffee's on me for the next month…" he grins at her.

"Don't tease me, Halstead! Y'know what I can do with the proper incentive." She laughs back at him.

"OH, I KNOW! Now go take it out on the pins." He winks at her and continues to watch as she walks away down the lane.

She turns to look back at him right before she throws. "I'm gonna hold you to this!" Right as she finishes saying it, she flicks her wrist and launches the ball down the lane; it curves at just the right time, knocking down ALL of the pins. She grins as she gets her first spare of the night.

"YES! THAT'S WHAT I'M TALKING ABOUT!" Antonio yells triumphantly as the partners high-five each other.

Now that it's Jay's turn, he tries to give himself some incentive too. His comes in the form of picturing the pins as how he felt anytime he saw Hailey with Adam… probably not the healthiest of ways, but it works. His next throw is a perfect strike... this time him, Hailey, and Antonio are loudly cheering and jumping up and down, leaving Kevin, Adam, and Kim staring agape.

Adam hits Kevin's arm, "You just _had_ to open your mouth, didn't you!?"

"I didn't know they were gonna go and do _that_!" Kevin exclaims.

"It's fine guys, we got this! They're still a ways behind, it'd be a miracle for them to catch up!" Kim gives the boys a pep talk as their opponents chuckle… famous last words in the world of sports.

With the final four rounds, Antonio maintains his level of expertise, and somehow, someway, Hailey and Jay manage to get a strike on each turn. They gaze at each other and grin after every one, almost as if they're telepathically encouraging the other; which doesn't go unnoticed by the other coworkers.

"Man, I see what you mean. No wonder you decided to break it off with her." Kevin whispers to Adam somewhere along their fifth strike. Adam just shakes his head in agreement back and gives him a "_Right_!?" look.

When the night is said and done, Team Upsteadson squeaks out the win by two points. None of them can believe it. But it's been great for Hailey and Jay because this was just the distraction they had needed from their earlier conversation. For a while, it even felt like things were back to normal between them… just two good friends having fun with their other friends. They don't go out in groups as often anymore, and this was good for them, at least for fighting their hidden feelings like when they're alone.

Once they got to Molly's, Antonio made a toast to the three of them, the first round begrudgingly off of Kevin's money… it's the last time he'll underestimate the power of their partnership.

"To a great team effort… especially to you two who really amped it up late, Voight would be proud, you guys really do make great partners!"

Hailey and Jay grin at each other and stare a beat too long as usual, trying to communicate silently all the things they wish they could say. Jay breaks out of it first, realizing Antonio is still waiting on them to clink classes.

"Cheers!" Jay says as Antonio turns to the others.

"And to the rest of you, thanks for talking smack… These drinks tonight are gonna be the best I ever had!" he jokes with them and gets fake angry glares from Kevin, Adam, and Kim.

"You suck!" Kim says laughing.

"Yeah, but not as much as you, apparently!" Antonio retorts, and all six of them crack up.

For the rest of the night, Hailey and Jay joke and chime in as much as they can. Both knowing they have some big decisions to make and things to think about soon… but for tonight, they're glad to have a breather from their harboring emotions…

* * *

_[A/N: Sorry for the delay, but April has been pretty busy for me and I honestly wasn't going to update any stories until the show returned... But alas, here it is anyway! Just a short, filler chapter to break up some of the angst. Hope you enjoy, & hope we get some good Upstead in tomorrow's (6x19) episode! I'm feeling good about them for the remainder of the season with the few little things I've heard. So cheers to hoping, and thanks for all the love!] _


	7. Chapter 7

Hailey and Kim were sitting at a local bar having dinner. It's been almost a week since Blair got killed. Despite Kim acting on all fronts that she was coping as well as could be, everyone knew it for what it was- a front. Hailey knew probably more than most, since she was the queen of pretending everything is fine (except for with Jay, she always confides in him); which is why she suggested this outing to Kim. If she's being honest, it's probably been therapeutic for both of them. The two have been enjoying their girl time, as it doesn't happen often… and getting it all in before they'll be joined by Adam and Jay soon. The boys overheard them discussing it, and naturally asked if they can join; Adam wanting to be there for Kim now more than ever, and Jay just wanting to be around Hailey whenever he could. The girls have until the boys wrap up their latest CI cases.

Kim has been picking her food and amicable all night, tentatively opening up to Hailey a little bit. They've never been overly close, as Kim just gravitates to Kevin, Adam, and Antonio more… and Hailey just took to Jay the most since she transferred into the unit. Sometimes it's just great to have a fellow female on your side though, the mentality can be more aligned at times.

"I think, what's getting to me the most, is my guilt if I'm being honest. My whole thing with Blair was just kind of weird, I tried my best to explain it to Adam last week… part of me was falling for him, but the other part of me was holding back." Kim states after beating around the bush for a while.

Hailey looks at her sympathetically, especially because boy, can she relate! Kim pretty much summed up Hailey's whole relationship with Jay all these years in one sentence. Completely different circumstances of course, but it certainly sounds eerily familiar. Hailey nods at Kim, signaling for her to elaborate on, knowing she's not finished with her thought.

"Don't get me wrong, I had a blast any time I was with him. And I guess if I thought about it for a long moment, I could possibly see a future when I was with him… but there was always the issue of our jobs. I mean, the guy worked for KELTON, of all people! He's practically Voight's #1 nemesis right now, and that says a lot since Voight has an abundance. I don't think I was ready to choose Blair over my career, or vice-versa, or even if we would ever be. The only person I ever came super close to risking my career for willingly and being okay with it was Adam… and we all saw how _that_ turned out!" Kim says sadly.

Hailey sits back and looks at Kim like she's her spirit animal right now. In all the years that Hailey's been on the force, there's obviously been a few job-related men she's dated… as much as she's hated it, it's hard not to with their line of work- you see and spend more time with your coworkers than anyone else, not to mention while risking your lives. There was the officer she dated while she was in the academy, which was intense, but brief. Then of course there was Garrett… which absolutely broke her when she lost him. She took a lot of shit for being with him, which at the time felt worth it… but losing him made her swear off romantic involvement with partners _at all costs_… something that was easy for her to stick to her guns with until Jay came along. And then Adam, which is laughable, because even though she cares for him, it was still something she foolishly fell into and would NEVER risk her career over him. Which brings her back to _Jay_, as always, and she knows if she truly takes the time to sit back and analyze everything, if it came down to Jay or her career… for the first time ever she's thinking she'd choose to have the former. _Wow_! Hailey's eyes widen slightly as that realization dawns on her. She never anticipated that _she'd_ be the one having an awakening while trying to console Kim. She definitely needs more to drink now that it's hit her like a ton of bricks that her feelings for Jay are even more complicated (and all-consuming) than she realized. But that's going to have to wait… right now her priority is to help Kim, and she's surprised by the advice she's about to give.

"Kim, it's totally normal for you to feel guilt right now, you just lost someone you cared about… no matter how much or which way you cared about him. You're always going to wonder what could have gone differently if the person lived longer. It's okay that you're not sure where you saw your future with him- it will NEVER change the fact that you cared about him in the present, and I'm sure Blair knew that. As for Adam… and I know this is going to be weird coming from me given the past few months… I wouldn't write the end of that chapter off just yet. Like you said, it means something that he's the only one you were 100% willing to risk your career for… and having spent more time with him these past months than I ever did before, I can say without a doubt that he's never once stopped caring about you. I saw how he reacted when we got kidnapped, how he's tried to be your rock this whole week… the world works in mysterious ways… We could probably all use a lesson that some things, some _feelings_, are just simply out of our control, no matter how much we want to fight them."

Kim slowly smiles at Hailey, eyes agape, in shock how much Hailey just said to her; and in retrospect revealed about herself. She takes a sip of her wine, gradually processing it all.

"Thanks, Hailey. It means a lot, you listening and being here for me! As for the advice, it sounds like you could probably use some of it as well." She knowingly smirks at the detective. Hailey gives her a soft smile back.

"Kim, and I say this with love: Don'T Even Think About It!" she waves her fork at her.

Kim chuckles as she looks down and moves some food on her plate. "I'm just saying!"

When Kim looks back up she see the boys coming in the front door and heading towards their table. "Oh, what do you know, you're saved by Jay again!" she laughs and points at the boys approaching behind Hailey's back.

Hailey turns around to see Jay and Adam making their way towards them. She feels the same familiar butterflies in her stomach starting that she can't control anymore any time she sees Jay. Yea, she's definitely going to need to start drinking something harder than wine now…

"Well, if it isn't our favorite girls from Intelligence!" Adam says as he grabs a seat next to Kim.

"You mean the _only_ two girls from Intelligence?" Kim says, bantering along like old times.

"You'd still be our fave even if there was a brothel of girls!" Adam winks at them.

"Oh, real nice!" Kim says shaking her head along with Hailey.

Jay slips down next to Hailey as this all goes on, rolling his eyes at Adam. "Hey." He says as he looks directly at her.

"Hey." She quietly responds, slightly blushing as her quick smile reaches her eyes. Kim glances at them with a perceptive look but doesn't dare comment.

With everything that happened with Blair this week, work had been super chaotic, and everyone wanted to be there to support Kim; so this was the first real time Hailey and Jay have spent together the past few days. The palpable tension obviously still simmering between them and getting close to boiling over.

"Did you guys eat yet?" Hailey says to both guys, hoping to alleviate the pull Jay has on her.

"Yea, we grabbed some Portillo's dogs on the way." Jay replies.

"Yea, I just want to drink at this point. You guys down to do a shot? I feel like we could all use and deserve one!" Adam asks. When Kim, Hailey, and Jay shrug and nod in agreement he flags the waiter over and orders a round.

The four of them spend the next hour or so trying to decompress and keep the mood light to help keep Kim's spirits high. It's something they've all needed after a completely atrocious week. Eventually Kim starts to slowly fade.

"I'm sorry to be a pooper guys, but I'm really tired. Hailey, is it okay if we leave now?" Kim asks.

Hailey is about to tell her 'of course' when Adam quickly chimes in.

"I can drive you home. I have to get to the precinct early tomorrow to write up reports. As long as you're cool to take Jay, Hailey?" he asks her as nonchalantly as possible, but the look on his face is blatantly obvious to her. She bites her lip trying to stop herself from shaking her head at him. Since when did Adam and Kim decide they want to be the death of her?

"Yea, of course I can take him, he's my partner… you guys get some rest!" she smirks at the former couple as they all say their goodbyes.

Once Adam and Kim leave, Jay and Hailey look around awkwardly for a minute, until Jay finally says; "Well, looks like it's just the Upton and Halstead show again… you wanna head out too?"

She shakes her head 'no' at him. "What I want is another shot, c'mon!" she stands up from the table and grabs his hand to lead him to the bar. Jay looks at her shocked, but doesn't question it. Something tells him he'll be driving Hailey's car tonight.

* * *

A few hours later Jay is inserting the key into Hailey's front door, letting them both inside. Hailey walks inside a little off balance… when she said she wanted shots, she meant it. He would have loved to keep drinking pace with her honestly, it's been a hell of a few months, but someone had to get them home responsibly. He's quite surprised Hailey allowed herself to get this way though, especially since she was the original driver… it shows him that 1) she must have really needed it, 2) she definitely trusts him explicitly to not only drive her new car, but count on him to get her back safe, and 3) she has to have a _lot _on her mind to give up this much control to alcohol; even on their worst days she's always restrained enough to not get _too_ drunk. He watches her make her way over to her liquor cabinet and is now completely baffled that she intends to continue, he realizes he should stop her.

"Woah, Hailey, what are you doing? Haven't you had enough for tonight? I know you won't get sick because you can drink like a sailor, but we do have to work tomorrow!" he uses humor so he doesn't sound too lecturing.

"C'mon Halstead, just one more, have one with me! I feel bad that you didn't indulge to get my ass home. Thank you, by the way."

He knows it will be useless trying to argue with her, and besides, he really could use one; so he shrugs his shoulders and agrees.

"Ok, but I'm pouring!" he says as he makes his way over to her kitchen island and grabs the bottle from her hand.

"You're such a cop, Jay!" she says, slightly slurred and laughing as she makes her way over to her couch and plops down hard.

Jay chuckles watching her amused and rolling his eyes, he's kind of enjoying this carefree version of her. They haven't had a lot of it recently. He walks into the living room with the two glasses in hand and sits down next to her. She positively beams at him as he hands her one of the glasses.

"See, I knew I liked you Halstead!" she says before taking a gulp of the tequila.

"Well, I'm glad I can make you happy with your own hard-bought liquor supply."

"No, seriously Jay, you should become a bartender."

That triggers the best laugh he's had in a while, considering he literally just poured straight from the bottle. "WOW! I should get you drunk more often… I've gotten more compliments from you tonight than I have in two years."

She frowns at him with a side-eye shaking her head. "Don't get used to it, mister."

"Roger that… but seriously, Hailey, anything you want to talk about? It's not like you to get this drunk, everything okay? I know these past few months have been…"

She cuts him off, "Can't we just have this Jay? Can't we just have fun for one night and not think about all the chaos?"

He nods at her, totally getting it. "Yea, yea, of course we can!" He sits back settling in and letting himself relax for the first time in a while.

Their first drink turns into another couple as another hour or so goes by. They attempted to play the "Heads Up" game on Jay's phone, which failed epically due to Hailey's drunken condition. Then they decided to have an old school Thumb War, where Hailey lost terribly in that too, irking her to no end and amusing the hell out of Jay. Finally they settled on some comedy movie on Netflix, Jay continually staring at Hailey, his heart aching… wishing he could tell her how he really feels… especially in this moment, she's just adorable to him tonight. Everything with Kim and Blair reminded him again of just how short life is, and he wishes he had the balls to act. During a lull in the movie, Hailey breaks the silence- even more drunk than before.

"So your double-date is this weekend right?"

Jay raises his brow at her, intrigued to see where this is going to go. "Yea…. Why?"

"No reason. Just curious. That'll be fun. You see a picture of her yet?"

"Yea, Will pulled up her Instagram for me to see."

Jay watches Hailey hesitate as she speaks again. "Is she pretty?"

He wants to tell her this girl can't hold a candle to her, but knows it's simply not the time. "She's attractive."

"That's good, I'm happy for you! You deserve some time away from work stuff…." She drifts off as she goes to take another sip of her drink, realizing it's empty. "Oh damn, looks like it's time for another!" she says as she starts to stand up with intent to head to the kitchen.

"Hailey, I don't think that's a good idea. You've definitely had enough for a Wednesday night."

"I'm a big girl, Jay, I think I know my limits ok?" she says as she starts to step over his feet… losing balance and falling into his lap. Their position now quite compromising. He grabs onto her so she doesn't fall off of him.

Their faces are inches apart as they stare at each other, the moment lasting excruciatingly too long for either of their states of mind, their heartbeats accelerating. Jay stares into Hailey's eyes realizing everything is right there for him for the taking. He thinks he's going to have a heart attack when he watches her eyes flutter close and lean in closer, in his haze registering her whisper ever so longingly…

"_Jay…_"

This moment breaks him. He knows she's drunk and vulnerable and despite every impulse of wanting to, he just can't take advantage of that now. Fuck! He hates that he's such a respectable guy sometimes, at least when it comes to those he truly cares about. He gently tries to set her back on the cushion and off of him.

"We should probably call it a night, Hailey… we have to be at work in 6 hours." He says as softly and gently as possible.

He watches her open her eyes to see them cloud over with hurt and rejection and he hates himself. He's hoping his only saving grace is that she'll be too drunk to remember the entirety of this situation tomorrow. She quickly puts her guard back up and agrees.

"Yea…. You're right… I should get to bed." She slowly stands up again with his help.

As she starts making her way to her room she looks at him casually and says, "You know where the blankets are, help yourself to the couch. I'll drive you to your place in the morning before work."

He wants to call after her, but knows it would be moot at this point in their state to talk. Instead he settles on silently watching her walk away from him, his heart breaking a little more with every further step. Neither realizing that that night, behind a single wall separating them (figuratively and literally), they're both lying awake for a while longer sulking over another missed moment… The world certainly does work in mysterious ways…

* * *

_[A/N: Figured I'd jam one more update in during the show's 100th hiatus week, lol. Full disclosure, I will probably be concluding this story before this season ends, as I've gone slightly more AU than I thought I would with the recent lack of Upstead. I'm hoping the show has some epic moments planned to cap the season though, it certainly sounds that way... & I'll continue on accordingly with my "Feelings" story per episode. Once this ends, I hope to continue more one-shots or another multi-chapter for Summer... *crosses fingers* to have good finale Upstead content to work with ;) Thank you so incredibly much for all the wonderful reviews, I'm so happy this story has resonated with you thus far!] _


	8. Chapter 8

**Conclusion!(?)**

Jay takes a break between gym sets to think about everything that's happened the past few days. He puts down the weight casually and leans back on the bench. Going to the gym in the early afternoon on Saturdays has become a biweekly tradition between Hailey and him. They thought it was a great idea in case they needed to work off any excess liquor calories from a rough or fun Friday night. He's extra grateful today that they still made the trip and Hailey didn't cancel on him given everything that happened between them the other night. If Hailey actually remembered anything from her drunken haze, she certainly didn't bring it up… although with her, that could go either way. Even if she was aware, it's not unlike her to pretend nothing happened. When they woke up to go to work that Thursday morning, she grumbled about having a severe hangover and being tired, but didn't say much else, except to yell at _him_ for letting _her_ drink so much. Typical. She stopped to get them coffee on the way to dropping him off at his house to get ready, but overall their ride was pretty quiet. He wouldn't describe it as awkward, but it definitely felt like there was an unspoken agreement among them to not mention the prior night.

By the time they got to work that morning, it was busy from the get-go. They didn't have a moment to breath and ended up working a near 13-hour shift with the case they had, which led into yesterday. Since Friday was so busy also, they certainly didn't have a moment to discuss their near kiss even if both of them wanted to, which he's confident Hailey did not. When they finally wrapped work last night, he had to get to that stupid double-date, so he didn't have time to talk to Hailey even if he worked up the nerve to.

Jay had begrudgingly gone on the date for the sole fact that he knew Will would have killed him if he cancelled. Luckily the night ended quickly because it was a complete disaster, and fortunately not due to his feelings for Hailey, or he'd have Will busting him again. No, it was a disaster because the girl was a complete nut… slightly due to Will himself, but both brothers wouldn't be seeing those girls ever again; which is completely fine by Jay… he only has eyes for one anyway, and she's currently getting off the treadmill and walking his way.

"What is this? You're tapping out already, Jay? Your poor wittle arms hurt from the big strong weight? I just ran 6 miles during this bench set of yours!" Hailey says to him teasingly.

He smirks at her while shaking his head. "We can't all be a machine like you, Hailey. But I do appreciate your half-Greek feistiness at 11am. Besides, these arms are anything but _wittle_!" he says while flexing, knowing it's going to get some kind of reaction out of her… hoping for a turned-on one if he's wishing.

She rolls her eyes at him, pleasantly over their exchange… Although if he is wishing, he does notice a slight hue rise in her cheeks.

"Alright tough guy, are you really done already, cause I still wanna hit the battle ropes?"

"No, I was just taking a quick breather. I should probably get some cardio in too."

"Ok, well y'know where to find me then." She says as she starts walking away, but then flips around again walking backwards. "Hey, you wanna hit Molly's tonight? I heard on the radio the new Lagunitas brew got released this week."

"Yea, sounds great, we can come back here tomorrow and work it off!" he jokes.

She scoffs , "Yeaaa… maybe you can, I'm actually getting in a good workout today!" and with that she walks fully away. Jay chuckles to himself as he makes his way over to the elliptical machine.

He's glad that nothing is awkward between them, that's the last thing he'd ever want. As he climbs the fake stairs, he looks on longingly from afar, watching Hailey at the ropes. She probably could kick half their asses if she really wanted to. He can't help but think how much fun that would be in the bedroom. He shakes his head, trying to get that image out of his head, at the gym of all places. The dirty thoughts have invaded his head even more these past few months as his feelings for her keep growing stronger. He knows he has to figure things out or confess soon, it's eating him alive. He raises the speed of the machine and tries to work off and metaphorically run from his thoughts.

They finally decide to call it a day at the gym an hour later after they did one of their last workouts together. He buys them both a protein drink before they head outside and start walking their separate ways to their cars.

"So want me to pick you up around 8 tonight?" he asks her.

"Sounds good. Or I can pick you up? I do owe you!" she replies.

"I've been waiting for those words to be said!" he teases and starts backing away before she almost hits his arm.

"But yea, that works… I'll even be ready and dressed for you by the time you arrive!"

"Well, that'll be a first… see ya, Jay!"

He chuckles as he watches her walk away, feeling pretty excited for whatever tonight may hold. Maybe he'll get them both drunk this time.

* * *

Hailey knocks on Jay's apartment promptly at 8. He's shockingly dressed and ready to go as promised. She can't get over how good he looks in his button-down shirt. Man, she's gotta get a hold of herself. She had a lot of time to think today after their gym session. She's incredibly grateful that he didn't bring up Wednesday night at all these past few days because as drunk as she was, she DID remember, and she was rightfully mortified. What was she thinking almost kissing him!? Despite the fact that her and Adam have been broken up for almost two months now, and the reasoning was thanks to _Jay_, he's still her _partner_ and she knows she's playing with fire. She finds herself caring about it less and less though, which surprises her, but it doesn't much matter considering Jay made it pretty clear the other night it was a bad idea.

She knows he always means well, especially when it comes to her, so she's not upset or angry. If anything, she's appreciative of a guy who didn't want to take advantage of her in a vulnerable state… she wonders if Adam had been the same way, if she would have gotten herself into _that_ whole mess still. Not that she has any ill-will towards him either; they both needed the comfort of someone else those few months they were together. She's really at a loss on what to do with her Jay situation now though considering she's lost her distraction from it. And the fact that they've been spending even more time together since the break-up isn't helping… but he went out with that dumb bitch last night so maybe their hangouts will be ending soon. _Ooh Hailey, jealousy is not a good look on you_, she thinks right before she hears Jay pull her from her thoughts again.

"Earth to Hailey? Come in Detective Upton!?" Jay says waving his hand in front of her face in his doorway.

"What? Oh sorry, I totally spaced out there for a minute!"

He quickly looks concerned before he turns teasing. "It's the button I left open on my shirt, isn't it? See, the gym makes me sexier after all!"

She turns her head in disgust and starts walking away. "Oh shutup, you wish! C'mon, lets go so we can grab a spot at the bar!"

He locks his door behind them and starts following her.

"You look nice too, Hailey! I mean, not as nice as this, but…" he says trying to rile her up again and keep the mood light.

"Yea, yea…"

The ride over to Molly's is a relatively quiet one, but not awkward. For once, Chicago is finally starting to warm up and they're enjoying the scenic sundown with the windows open. It's enough to clear both their heads and ease any jitters either of them may have.

When they arrive at Molly's they sit in their usual corner spot at the bar, waving to a couple of acquaintances along the way. Hermann is the bartender and he beams when he sees them.

"Well, well, if it isn't my two favorite detectives! What can I get you guys?"

"Hey Hermann! I'd love to try the new Lagunitas if you still have some." Hailey replies.

"I'll have the same." Jay seconds.

"Excellent choice, coming right up. It's been selling like hotcakes! Chicagoans love their hometown beers!"

"Thanks Hermann!" Hailey says as he comes back over with their beers. They clink their glasses together as Hermann walks away to serve others and take a sip.

"Wow, this is really good!" Jay says looking impressed.

"Yea it is… you may have to drive again!" she says and laughs at Jay's shocked reaction. "I'm kidding!"

"I was gonna say… that would become quite the habit if so… not that I don't thoroughly enjoy seeing you as a carefree drunk!"

She rolls her eyes at him and does her best to change the subject. "So that case this week was pretty crazy huh? "

"Yea. I'm just glad we wrapped it before the week ended. I was in no mood for more OT."

"Seriously…" she says painstakingly agreeing.

They make small talk for the next hour, completely trying to avoid conversations that are inevitable. As much as she doesn't want to know, she knows she _needs_ to know how his date went last night. She's fairly certain he didn't hookup with her yet at least, considering he made it to the gym.

"Soo… how'd your double date go? It was last night right?" she says while picking at the wrapping on her bottle, trying to feign how curious she really was. He suddenly bursts out laughing and she looks at him genuinely confused.

"Oh, it was atrocious!"

"Oh?" she replies a little too excitedly.

"Yea, it was pretty much over before it started. We all barely made it through the meal. Apparently the girl Will was trying to set me up with is extremely political, as well as politically-correct… and Will, of course, made some off-colored remark that just set this girl OFF! Her and her friend decided to leave before we even got the check. Needless to say, we won't be seeing those girls again!" They both burst out laughing, Jay reliving it and Hailey imagining it.

"Oh, I'm so sorry!" she says between the laughter tears.

"No you're not!" he smiles back.

"Yea, you're right! That's too funny to be sorry about."

"I feel sorry for Will, he's the one who wanted to go… but he brought it on himself."

"Well, if it's any consolation… the girl probably didn't deserve you!" she realizes how that sounds and finishes, "…or Will either!"

Jay turns his body on the stool to fully face her and leans his arm on the back of her stool, staring at her teasingly.

"Why Hailey, if I didn't know any better, I'd think you were jealous…"

She playfully pushes him. "Yea right, Jay, in your dreams!"

It's then that Hermann comes back over to check on them and gives a knowing look.

"See, I told Adam you guys would eventually work it out on your own!"

Jay turns and gives Hermann a bewildered look, while Hailey looks away absolutely horrified.

"What do you mean, Hermann? Work what out?" Jay asks.

Hermann looks at Hailey and realizes his mistake. "Oh, fffffuu…" he mumbles shaking his head. "Man, Cindy is always telling me my big mouth is what makes people not want to have a normal bartender/patron confidential relationship with me like they do with Stella… I'm just gonna go check on my table over there and give you two a minute!"

"Hailey, do you know what he's talking about?" he asks her, still trying to figure it out.

"Jay… can we just drop it, _please_!" she pleads with him.

"I just don't understand what Adam would be doing talking about us to Hermann."

She stares into her beer bottle and sucks in a breath.

"I may not have been entirely honest with you on why Adam and I broke up…"

"What do you mean?"

"Adam broke up with me because he thought I had feelings for _you_, that I wanted to be with you, and he thought you felt the same way…"

Jay looks taken aback. "Do you Hailey… have feelings for me?" he asks quietly.

"Jay…." She warns trying to get out of it, but finally gives in, it's all been boiling down to this anyway…

"Yes…" she whispers and he gives her the same look he did when she told him she'd follow him blind. "But it doesn't matter, we're partners, and I get if you don't feel the same…"

"Hailey…"

"No, I can't do this here… I have to go…" she says abruptly, holding back tears before she hops down from the stool and runs outside.

She manages to almost make it to her car before Jay catches up to her, cornering her along the building wall. She has to get away before she completely breaks down. She tries to break out of his arms holding her. This is soo not how she wanted it to go down, but she was the one who told Kim that the world worked in mysterious ways. _Idiot_.

"Hailey! Can you stop fighting and just let me talk for one second!?"

She looks up at him through the tears and braces herself for whatever he has to say.

"If you weren't so busy trying to fight having feelings for me by being with Adam, you'd have realized that I have feelings for you too. It broke me seeing you with him! And I was so happy once you told me it was over… but I figured you deserved time." he finally gets off what's been on his chest for months now.

She looks up at him shocked, not fully believing it, but elation quickly setting in.

"You do?" she manages to gasp out.

"God Upton, do you always have to be so stubborn!?" his voice sounds scruff when he says it, right before he crashes his lips onto hers.

It takes her a second to process that Jay is finally kissing her, but she responds in kind soon enough. They've both been waiting and dreaming of this moment for so long and it's been entirely worth it. She clings strongly to his neck, pulling him even closer as she runs her hands through his hair, earning her a groan from Jay. He presses her hard in to the wall and it crosses both of their minds that they need to leave soon before one of their coworkers has to arrest them for public indecency. Jay breaks away and they're both almost out of breath. They take a moment to just stare into the others eyes like they always do; this time fully knowing the loaded emotions that lie behind them.

"Soo _Detective_… you wanna come swap stories in the back of my van?" he asks her with a huge grin.

She beams up at him, fully realizing the throwback he's bringing back up and wanting to play along.

"I don't know, I could get fired… I'd much rather swap stories in your bed for the first time…"

They giggle with each other, positively enjoying themselves and realizing that everything has been leading them to this moment… if any two people were ever fated to be, it was them… while the road was long and winding, the ride was certainly worth it…

* * *

_[A/N: Since we had a conclusion to the Upzek story line this week, it's only appropriate that I give a proper conclusion to our Upstead loves as well... at least in this story. It's brought me such joy to see how much this story has resonated with you, as I didn't know how far I could take a mulit-chapter. Fortunately, I've made the time again to dedicate to writing, and it means so much to me that you've followed along thus far. Thank you from the bottom of my heart for all of your kind reviews and likes... I hope you enjoy this epilogue. I'm certain now it's the end, but I also know to never write anything off the table (no pun intended :p) Until next time, I hope this makes you as happy reading it as it made me writing it!] _


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